Wiggins attended East Boston High School in East Boston, Massachusetts and was a letterman in football and basketball. In football, he was an All-City and an All-League honoree. In basketball, he helped lead his team to the state championship as a junior. Wiggins graduated from East Boston in 1993. After high school, he attended Bridgton Academy in North Bridgton, Maine for a year of post-graduate study. In 2011, East Boston High School honored Wiggins by retiring his jersey.[1]

Wiggins attended Marshall University for two years before transferring to the University of Georgia. He led Marshall in receptions in 1995 with 54 catches for 681 yards (11.1 yards per catch) and scored four touchdowns in helping Marshall to the finals of the I-AA Championship, falling to Montana 22-20. He also played as a freshman in 1994 (5 catches, 56 yards and 1 TD - 11.2), when Marshall advanced to the I-AA semifinals, losing at Boise State, 28-24, and winning its first outright Southern Conference championship (second of three SC titles for the Thundering Herd). When MU head coach Jim Donnan took the Georgia coaching job, Wiggins and teammate Olandis Gary transferred to the Bulldogs, sitting out in 1996 and playing in the SEC in 1997 and 1998, winning bowl games both years with UGA.

Wiggins played in New England for three seasons (2000 - 2002). While in New England he won Super Bowl XXXVI in 2001. After a quiet 2001 regular season in which he only caught 14 passes, Wiggins became a key part of the Patriots air attack in the playoffs. Wiggins is perhaps best known by Patriots fans for his 10 catch, 68 yard performance in the Patriots AFC Divisional Round overtime victory against the Raiders. He also caught a seven-yard pass in the Patriots final Super Bowl drive that enabled the field goal kick to win the game. He also became famous for wearing red cleats.

Wiggins signed with the Minnesota Vikings, spending three seasons with the team (2004–2006), before being released on March 1, 2007. Minnesota is also where Wiggins was known to be a part of the Love Boat Scandal.

Wiggins has ventured into sports media upon retiring from football. In 2010, Wiggins obtained various positions in Boston sports media outlets such as CSN New England, WBZ, and WHDH. Until August 13, 2014 he frequently appeared on 98.5 The Sports Hub alongside Michael Felger and Tony Massarotti.[3] Though he is primarily utilized as an NFL analyst, he also covers other Boston sports news.[4] Wiggins appeared on A&E's Flipping Boston, the "Flip or Fumble" episode which features Wiggins joining hosts Pete and Dave on the renovation project of a home. Wiggy currently co-hosts a morning show on a local Boston hip hop radio station 96.9.